How many times have you wished for a personal assistant? Someone to pay the bills, schedule the doctor visits, put gas in the car?

You can’t talk to Amy Cray without wishing she would come to your house and make everything easier. She’s just that kind of person—with an easy smile and a competent, friendly manner.

She’s also the personal assistant for, among other clients, a Very Famous Literary Personage. Personal assistants of Amy’s experience make $80-$125K annually, plus health, retirement and bonuses, but those positions are hard to come by. Amy is in the middle of that range. Personal assistants with moderate experience working for CEOs, CFOs, etc. generally make around $60K.

Amy grew up in the mountains of California, in a town of 80, with parents that were, as she puts it, “not pop culture hippies, but real ones.” She left at 18 and moved around the west coast, nannying and cooking to pay the bills and support her music career. That gradually turned into jobs running the households of people with, as she said, “tons of money.” Now 38, she lives in the Bay Area with her wife and two young children, and has a blog.

I was curious about what it was like living with the rich without being one of them. Here’s the edited version of our conversation.

How does it feel working for people who have so much more money than you do?

It’s so crazy. It’s really interesting. So my wife: The majority of her career has been in nonprofit and she does work to support homeless and low-income families. So we always say we actually do the same thing. But she does it for people with no money. And no house.

Who gets paid more, you or your wife?

Oh, me. And that’s sort of a family choice, to split the difference.

I’ve worked for globalizers before and felt like was I was helping make the world a worse place, and kind of felt that guilt. This is a personal thing—I don’t find this a lot with PAs—but I need to know that the life that I’m supporting is doing something good for the world. If I’m spending time away from my kids and away from whatever other priorities I might have, and working really hard, I need to know I’m doing it for somebody who deserves it.

Then again, a lot of it is frivolous and superfluous, and “Oh, can you book the tickets to Dubai?” And so we’ve always felt that it’s a comfortable equality for our family if she’s like, working to “save the people.” It evens out a little bit.

Is it weird dealing with such big sums of money like you do?

I carry my clients’ credit cards with me because I purchase on their behalf all the time and so for me it’s just completely normal to be like “charge that $6,000″ and not even think about it. And it is very strange because it does seep into your life—your normal life. Like, I’ll write people’s tax checks for $400,000 and just the act of writing “400,000″ on a check—having had that experience! Even if it’s not your money.

There’s a little bit of ownership that sort of seeps in.

I can see that.

That creeps me out every once in a while. Like the bonuses. We’ll talk about holiday bonuses. “How much did we give the housekeeper last year?” And that’s a normal thing for me to say. And then later I’ll be like, oh my god, that’s crazy. Part of that is just because it’s such intimate work. It is your life, in a way.

But yeah, the spending thing is strange. I see that being confusing, actually, more for my family than for me. Because I sort of come home with those experiences: Like, oh, I just packed so-and-so off to Paris for Christmas. Like a client bought a $90,000 car one day just for his wife, for fun, just “Happy Thursday!” And me coming home and saying, “I took the new BMW out for a spin. It was super fun”—my family is kind of like, “What is this life that you live?”

And for my daughter especially cause she’s like, “Well those kids all have iPads, and why did they get to go to London over spring break and we went to nana’s house?”

What do you tell her?

She’s never said anything to indicate that she feels she deserves that too. I think she does get the concept that these kids live a different life than what we live, and they have the kind of money that they can just do stuff like that all the time. She also knows that they aren’t any happier than we are.

Because you spend large sums of money, even if they’re not on your own behalf, do you get that special kind of treatment? That different way the rich are treated?

You sort of have access to that world. That’s actually very true.

I also do know what kind of power that wields, whether it be name-dropping or access to money or knowing that we could make things difficult for a vendor, if they really screwed us over. People would listen.

Do you ever get jealous, not so much of the money but of that ability to get things done?

I feel like my clients are usually about 20 percent less happy than anyone I know in my income bracket.

The perk of being able to throw money at something—that’s amazing. I love that. You problem solve by throwing money at it. And that’s the kind of thing that I’m like, “Ah, that’s so awesome, you just take the credit card and make his problem go away.” But I’m never jealous of it because I feel like ultimately that doesn’t outweigh the benefit of having either more time with the people who really love you, or access to people who you know love you for you, not because you’re famous.

As a musician yourself, do you like working for other artists or does it make you wish you could make money off your own art instead of being a PA?

That’s a funny question because what I’ve learned is how hard it is for almost anyone to make a living off of it. It doesn’t make me feel better or worse. But people in the fringes of my Bay Area family will mention, “I want to write a book” and I’ll be like, “Oh no, no, no, god, no, don’t. You don’t want to get into that.” Because I see how hard it is. It’s impossible. It’s hard for people who are really good at it and do it very well. In my current position I know so many writers in various stages in their careers and varying degrees of talent, as well as people who are world-class, phenomenally incredible writers—we’ll have coffee with them, and they’re around. It’s hard for those guys! You don’t really ever know when you’re next paycheck is coming.

Even when you’re at the top of the heap?

It’s still super-stressful. Specifically for writers.

What makes a good personal assistant?

Loyalty is huge. You cannot have someone in this position—in positions like the ones I have nowadays—who doesn’t come with incredible recommendations, because you’re placing them in control of everything. They know more about your investments than you do, they are managing the other people that help you, whether you have nannies or people working on your house or people who are interacting with you in your work life, and running your career. If you have a point person like that it has to be someone who’s been doing it a long time.

So this kind of job—is it salaried?

The good jobs are salary. The part-time jobs and the ones where you’re not an integral part of daily operations are hourly. The holy grail is a salaried job with a 401(k). It’s like a whole corporate structure. That’s the thing that PAs, professional PAs, go for: that kind of job. Usually there’s travel, sometimes there’s housing provided.

Are you where you want to be in your career? Is being a PA the job you want to do forever?

I’m kind of at the point where I could stay at the level I’m working at now. I could pretty much work for anybody, except for billionaires.

There’s a huge jump between the two. There’s this kind of money and there’s that kind of money. But that’s really distinctly separate by what kind of network we’re talking about. People who are billionaires—they have a staff of MBAs working on their team and you could be one of those people. And I could do that. I don’t know that I want to, because it’s managerial. It’s not as personalized.

Right now I feel like I’m absolutely doing the thing that I should be doing. Whether or not I feel like that in six years, we’ll see.

“I was curious about what it was like living with the rich without being one of them.”

Maybe this should say “super rich,” because I’d consider ~$100k/year to be pretty affluent, especially since that’s almost double the median household income in California (and $100K is only one earner!). But then again I guess it’s all relative.

@therealjaygatsby So I’ve seen this discussion so many times before on this site before, but is that “rich”? Maybe upper middle class? Her wife works in the nonprofit world working with low-income people so her salary is probably not that high. And they have two children.

If one person earning $60K pairs up with another person earning $60K and they have two children, and a combined household income of $120K. Are they now rich? I think they are relatively rich to low-income families, but not the 1 percent I think of when I think about rich people (I think the figure is something like $370,000 to make it into the 1 percent).

@EDaily Like I said, it is relative. But I think it’s a mistake to compare your own income against that of the 1 percent. After all, they represent only 1 percent of the entire population. Compared to the vast majority of households in the country, $100k-150k is indeed quite well-off (or, dare I say it: rich). I think we need to adjust our idea of what exactly “rich” means in this country. As I said before, I’d consider the 1 percent to be considered “super rich” or, as @seaermine puts it, “Scrooge McDuck rich.”

@therealjaygatsby Seriously. I make $19k a year, $100k is basically Scrooge McDuck rich, to me. And as someone whose mother raised her on about $22k/yr, over $100k to raise two kids is MORE than enough. Please.

That said, they are in the Bay Area, and my tiny brain cannot wrap around real estate/rental prices there, so they could easily be upper middle class in that area. Depends.

@EDaily I believe that 100k (combined household income) puts you in the top 20% of incomes in the US. Which, is more than just the upper middle (I mean, would the second apple in a pile of 10 apples be upper middle or top? I’d say top). Just because other people are richer doesn’t make her less rich. Also, that’s just her income, even if her wife only makes 30k (which, I’m guessing she makes more) she’s still rich.

I don’t think kids really affects it at that level, my parents raised two kids on a lower salary than what they have (including in expensive areas) and we were still rich, even though we didn’t have a private jet. And it’s totally possible to be rich and still be amazed at how other rich people live. I make about 40k, feel very well off, but would be amazed by someone who makes 100k, that person making 100k would be amazed by a family earning 200k, that family would would be amazed by 500k, and that person would be amazed by someone making 1 mil…etc.

@therealjaygatsby How much is enough really depends on where you live. 100K is awesome in most areas of the US, but in SF/DC/NYC it can still feel like a stretch. Also depends on family size and need, and needs for the area. For example, when I did my fellowship out in Palo Alto, everyone was living paycheck to paycheck on 65K + housing stipend. As a single household of one, I lived pretty well, but had never dealt with recurring expenses related to owning a vehicle, which threw my budget off.

My friends with kids though struggled, because the avg rent then (it is now higher) was about 2K a month for a fairly basic one bedroom. It wasn’t uncommon for 3-4,000 to go to rent alone, then taxes on the money, and that’s two thirds of your earnings.

Now that I am home in DC, my hubs and I live well on our combined incomes, but having a kid throws all of that financial security out. Just looking at adding daycare (anywhere from $200 – 500 a week, depending on how nice it is) takes our nice salary to an ok salary. We are very fortunate. But in places where most of your neighbors are putting up $200k-300k a year and still complaining about being financially insolvent, it’s hard to view the dollar amount objectively.

Wikipedia says median household income in San Francisco was just about $70K in 2011, and almost $85K in Santa Clara County.

I don’t think household income around $150K in an expensive area makes you rich. And I think there’s a decent gap in between “more than enough” and rich. But possibly that’s because I’ve always been at least middle class and have never felt rich.

@therealjaygatsby we also have to consider taxes.
eg: husband makes 60k, wife makes 60k. Each person is in a certain tax bracket and would bring home more money after tax than if it was just the husband or just the wife earning 160K on their own – the tax bracket on 160K would def be a lot higher, leaving them with less take-home pay to live off.

@Latoya Peterson@facebook Daycare, Jeeeezus. Yeah. The place associated with my former employer (in downtown/FiDi SF) was $3,000/mo for an infant. Three thousand dollars. Per month. Little wonder that I found other options while my older kid was a baby/toddler, then quit when I had another, because after daycare I’d’ve cleared about $125/month from my not-small paycheck — forget mortgage, food, utilities, clothing, etc.

@Gleemonex The president of Barnard was talking about that on Fresh Air! (Because of writing a book about working women’s stuff, but I haven’t read the book…) About how women leave/pull back from the workforce when they have a SECOND child.

Maybe other people aren’t interested in this so much, but next time I would be interested in more of a daily run down. Is this a demanding job? What does she fill her time doing? How did she get started?

Great interview, though I too would have liked to know more about what day-to-day life is like for a PA. I’ve nannied for wealthy families so I know a little bit about what goes on. The hardest part for me was doing the grocery shopping and having to consciously NOT shop for sales or the best deals, because rich people don’t care that the store brand toilet paper is half off. They want to best everything regardless of price.

@sherlock For the wealthiest family I worked for, I basically ran the house because the parents were so busy at work (mo money, mo problems). Groceries, errands, laundry, cleaning between the cleaning lady’s visits. I was a jack of all trades really. And no I did not get paid enough for it.

not to be a wet blanket, but saying “a famous literary personage” involved with homeless outreach in the bay area is a bit like that gag on the simpsons. “Let’s call her… Lisa S. No, that’s too obvious. L. Simpson.”

@pissy elliott Oh, I see where you were going. So relieved to know I’m not the only person for whom the very interesting subtext of this piece the FLP was. I was going to guess Danielle Steel, which seems to fit with Dubai.

Ha! I’m a PA, too, but “entry level” or whatever–seven months in. A lot of what she said totally rings true. Writing checks for hundreds of thousands of dollars really is a trip, and I totally have this weird lifestyle creep based on seeing exactly what my boss spends on what.

I suspect different PA’s days are totally different than others, depending on what the boss does and what other staff he or she has access to. For me, my boss manages several rental properties, so a lot of what I do is basically “office manager” type work for that, and I do bookkeeping to separate those expenses from her personal expenses. But, you know, I also take the car in for inspections and go to Nordstroms and organize her vacations and pay bills and once I baked a pumpkin pie. Oh, and her husband steals me all the time to do random things for him, including dealing with the lawyers working on his late mother’s estate. It’s a pretty cool job, tbh.

I, too, would like to hear more about what her daily duties are and how she got into the business. Also, does she PA for just one person at a time? “I carry my clients’ credit cards with me.” That sounds like she concurrently works for 2 or more. I am interested in how she is treated and what the hours are-is she on call 24/7 and expected to drop personal engagements to do something for the employer?

This whole subject is fascinating to me! My first job when I moved to the Bay Area in 1998 was in the office of a high-end home staffing agency. In the 18 months or so that I worked there, I discovered a whole different world than the one I came from (small-town Texas, nooooo money) and even than the one I’d gone to college in (Columbia). One of our most famous clients had this insane huge mansion in Pacific Heights, with a staff of about 10 full-time (PAs, housekeepers, cooks, nannies), not to mention the ass-army of part-timers and weekend/holiday/evening coverage people, and had bought the house next to theirs for the nannies AND THE NANNIES’ NANNIES to live in. And it wasn’t just the money our client roster had — it was what they wanted done, what they wanted the help’s backgrounds to be, the code words the industry used (a thousand times I heard my boss say on the phone, pitching candidates to clients: “She does have English as her first language,” i.e. “she’s not Hispanic”, or “Oh, she’s the cute cheerleader type,” i.e. “she’s young and white,” or “A very warm, motherly type, loves babies” i.e. black or Hispanic). Crazytown.

@Catface You know that’s right. Bleccch. I can’t believe I lasted as long as I did (for this and many other reasons … what a poisonous place to work). Thank Shatner for the rising tide of the tech boom right around then, eh?

I’m a PA for a wealthy couple in NYC and I just fell into it. I’d be so curious to meet other PAs and commiserate, exchange ideas, etc. and find out how they got into the field. My family and friends are all fascinated by my job but sometimes it’s actually pretty boring. There are lots of perks though, especially since the wife and I wear the same size clothes and shoes, so I get really great hand-me-downs.

@Nerdalie That’s pretty much exactly what my situation is like. Got the job randomly off of craigslist, and my friends are jealous/perplexed but also confused about what I do. I live in Austin, though. That’s awesome about the shoes and clothes! What do your rich people do?

@moreadventurous He’s in finance and she’s an artist. So I get to do creative work along with the other tasks. I studied photography at art school and never intended to have this type of job but I’ve had a lot of time and flexibility to work on my own projects so I’m ok with it. Besides, I think I’m better off being able to work on whatever photography projects I want rather than shooting for a living. Or that’s what I tell myself, anyway. ;)